Harold Ford Jr. faces several obstacles in his potential bid to challenge Sen. Kirsten Gillibrand for the U.S. Senate seat she was appointed to in January 2009. He’s a carpetbagger, arriving only recently in New York after building his career in his native Tennessee. He’s a Blue Dog Democrat in a state with a strong liberal base. And, perhaps most importantly, he’d have a tough time raising the scratch to challenge Gillibrand—a champion fundraiser sitting atop a war chest of some $5 million.

Ford, a longtime U.S. House member who lost a 2006 bid for the Senate in his home state, moved to New York, got a job with Merrill Lynch, got married after a long and storied bachelorhood—and began eyeing a run for higher office. In between appearances on MSNBC’s cable chat shows, he began flirting with the idea of challenging Gillibrand, a two-term House member from upstate New York appointed by Gov. David Paterson to fill the unexpired seat of now-Secretary of State Hillary Clinton.

The metropolitan area that donated the most to Ford's 2006 Senate campaign was New York City, with $2.25 million vs. $1.39 million in his home base of Memphis.

Gillibrand is widely seen as one of the more vulnerable Democratic incumbents in the Senate up for reelection this fall. And New York City Mayor Michael Bloomberg, a billionaire, has recently met with Ford, to explore the possibility of his candidacy and express frustration with the incumbent’s voting record.

Still, Gillibrand is no easy mark. She enjoys the
support of the White House, and she has a powerful ally in Sen. Chuck Schumer, one of the state’s most influential politicians and one of the country’s most effective fundraisers.

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Richard Wolffe: Why Obama Can’t Stop Meddling “[Ford] definitely starts at a disadvantage,” veteran Democratic consultant Hank Sheinkopf told The Daily Beast, regarding Schumer's support. “There aren't many places you can go—real estate, finance. You have to find somebody to lead the charge in each of those sectors and it's easy to cut them off.”

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John Avlon: Shameless Haiti WingnutsFord is no slouch at fundraising himself. In 2006, he amassed an impressive $14.3 million in his bid against then-Chattanooga Mayor Bob Corker for Tennessee's open Senate seat,
according to the Center for Responsive Politics. Although Ford ultimately lost, the money helped him stay competitive as a Democrat in a conservative state, against an opponent whose $18.8 million haul included more than $4 million the Republican candidate loaned himself.

And the Memphis-to-Manhattan transplant does have high-rolling friends in Gotham City.
News reports suggest he may be able to turn to the likes of investor Steven Rattner, HBO executive Richard Plepler, and Bloomberg to help finance a primary run.

Ford's finance chairman for his previous Senate run, Charles Robert Bone, told The Daily Beast that the former congressman's networks of donors might translate beyond state lines as well.

“I think he is a prolific fundraiser and I think he would be able to raise money across the country,” Bone said. “I don't think he's going to be deterred by what Gillibrand has raised to date.”

About $2.38 million of Ford's donations in that election cycle came from New York state, according to the Center for Responsive Politics. The metropolitan area that donated the most to his campaign was New York City, with $2.25 million vs. $1.39 million in his home base of Memphis.

“If Harold decides to run, he'll be confident, as in the past, that he'll raise the money required to win,” Davidson Goldin, a spokesman for Ford, told The Daily Beast.

But Ford will need to call on all his fundraising skills if he hopes to unseat Gillibrand, whose camp says they have raised $7.1 million over the last year and have about $5 million in the bank.

“We'll let them make their own calculations,” Matt Canter, a spokesman for Gillibrand, said of the Ford campaign's claims. “Kirsten Gillibrand has received tremendous financial support because of the terrific job she's doing as senator.”

Still, Sheinkopf, the longtime New York Democratic strategist, says Ford’s chances could be boosted by the general popular disgust with incumbents in New York, especially given that four statewide officials, including Gillibrand, are unelected and either replaced scandalized officeholders or were appointed to fill vacant positions. Ford's team has emphasized his “independence” from the state's political institutions and Albany's unpopularity would likely form the core of his campaign.

However, Doug Muzzio, a political-science professor at Baruch College, said that Gilibrand's early fundraising advantage, further buoyed by support from national women’s groups, may be too much to overcome.

Gillibrand's left flank has typically been considered her weak point, but Ford has built a reputation as one of the more conservative Democrats nationwide, which makes him a somewhat unexpected potential candidate. However, Ford has been tacking to the left in recent days, softening his position on immigration, gay rights, and abortion. He recently announced his support for gay marriage after
previously backing the Federal Marriage Amendment in Congress while his apparent conversion in favor of abortion rights after previously identifying publicly as “pro-life” has
prompted attack ads from NARAL.

Gillibrand has raised eyebrows with her own shifts on
immigration and
gun control since moving from a conservative congressional district to statewide office, which could complicate her attacks on Ford.

According to Sheinkopf, advertising dollars could be the key in determining which candidate's “flip-flop” attacks stick with voters.

“The difference is she has $7 million in the bank and Ford has 22 cents,” he said. “He or she who has the dough is the one who can fire the gun.”

Benjamin Sarlin is a reporter for The Daily Beast. He previously covered New York City politics for The New York Sun and has worked for
talkingpointsmemo.com.